Cowgirl's Outhouse
by Discreet Kitty
Summary: Set During S1 E21: A Doll's Outhouse. After Jessie overcomes her fear of port-a-potties, she meets a familiar looking teenager that helps her overcome her dry spell ... inside the port-a-potty.
1. Chapter 1

**Disclaimer: I don't own Jessie and I also didn't come up with the idea for this pairing. This story was requested by 27. Enjoy!**

Jessie Prescott stood in Zuri's bedroom, staring at the blue portable toilet as she considered what Darla would say if she told the bitch that she slept inside a port-a-potty the night before. She shook her head as she realized how her life now involved sleeping on toilets. This wasn't the life that she wanted for herself. Before Jessie arrived in New York, she had dreamed of starring in Broadway plays, filming television shows, or singing on stages. The eighteen- year old Texan never imagined herself being the nanny of four adorable kids or being hired as a nanny by a movie director and a fashion designer. She definitely didn't assume that sleeping in port-a-potties was part of the many roles she had to perform as a nanny.

"It feels like a _potty_ every day," she joked to herself.

She was glad that none of the kids were around to hear her joke. The girls were spending the morning at the apartment complex's spa and the boys were in their room doing _who knows what._ For the first time in the last few months, Jessie was finally alone. This was the first time that she was actually grateful to be alone. As long as she could remember, she was always by herself - alone in her bedroom, a hermit in school, or in solitary at the military base. Her father was either too preoccupied with training or too busy serving overseas to spend any time with her. When it came to friends, her father's occupation prevented her from having any. The only person she had growing up was Darla but Jessie could never consider the deadpan bitch a friend.

Once Jessie started high school, the only remedy for her loneliness was boys and she quickly built a reputation with them. The jocks labeled her as a single serving of a southern belle. The bad ass drama kids affectionately referred to her as "flying over brazil for the night." The techies introduced her as Fort Hood's overnight wife. Sometimes when she saw a lover in the hall, he would point to her and whisper to his buddy that "he took a ride on the town pony." The boys' nicknames didn't bother Jessie as much as the ones the girls called her. The environmentalist girls called her a "cum depository," the cheerleaders labeled her as a "skeet guzzler," and the ultra conservatives just stuck with the term "slut." Despite the small variance in jargon, everyone agreed that Jessie was a whore.

Her promiscuity had nothing to do with manipulation, popularity, or vanity. She hated waking up in the middle night, turning over and seeing that the other side of the bed was empty. She liked laying her head against someone's chest, cuddling up against them as they stroked her hair. She knew that the guy would leave her the first thing in the morning, ignoring her when she walked by him in the halls and forgetting their relations when he flirted with someone else right in front of her. She cried herself asleep on the nights when she texted an old flame and he wouldn't reply. She would leave messages on his phones, singing Taylor Swift songs while she played a few strings on her guitar. The only thing that made her feel better was when she walked around the base a midnight, spotting one of the solider's son. Before she knew it, his hands would be unbuckling his pants and yanking off her cotton undies. It was a vicious cycle that was broken the day a cute little six-year-old girl found her lying on the sidewalk.

 _Gutter whore_ , she thought as she imagined what Darla would say if she found out exactly how she found her job.

To Jessie, it was irrelevant if Zuri approached her and offered her the job. What mattered was the fact that she was no longer alone. In fact, she could never be alone. The past few nights, Zuri had kept crawling into her bed and waking the older girl up when the younger girl tossed and turned. Jessie usually would pleasure herself before she went to sleep but now Zuri made that impossible.

Now since the kids weren't buzzing around her, Jessie could finally take care of her needs. She stared at the port-a-potty and wondered how long it would be before Tony's buddies came to move it. She had just overcome her fear of being in portable toilets and the only way Jessie could think of to celebrate was to "paddle her pink canoe" inside the tiny bathroom.

She touched the waistband of her black high-waisted skirt, making sure that her cellphone was still properly stuck between her navy blue blouse and the elastic band of her skirt. Out of habit, she glided her fingers up to her chest and over the swell of her breast. She could feel the small package wedged between her black bra and her C cup sized breast. She knew that it was stupid to always keep a condom inside her bra since she no longer had the time for the type of frivolous sex she had during high school. Still, she always liked to feel prepared for anything. She opened the plastic blue door, stepping inside as her black heels made a clink. She closed the door so fast that her skirt got caught in the door's cracks. When she re-opened the door, she noticed that there was an unfamiliar teenager standing outside.

"Who the heck are you?" she sputtered.

She stared at the boy, his brown eyes were leveled with hers. He flashed a smug smile, showing off his perfectly pearly white set of teeth. Jessie assumed that his teeth were too perfect to be natural so he must have had braces when he was younger.

 _Rich kid_ , Jessie thought as she scoffed out loud. _He must be one of Emma's little boyfriends._

She had to admit the kid was handsome. He had slicked black hair, brown eyes, and tan skin. He looked like he spent a lot of time in the sun. Automatically, that made Jessie feel that the boy wasn't the stereotypical arrogant, rich boy that lived in Manhattan. He looked down to earth, active, and probably spent a lot of time playing sports. In fact, he looked like a boy that Jessie could of went to school with. She noticed that he was wearing a plain gray t-shirt and blue jeans. He definitely wasn't one of Emma's friends and Jessie imagined that Emma probably thought the boy was beneath her.

"My dad wanted me to tell ya that he's running late," he said as he eyed Jessie up and down. He sounded like he was from New Jersey, only confirming to Jessie that he wasn't one of Emma's friends. He was definitely like one of the boys from Jessie's high school. Most boys tried to wait until the girl wasn't looking to check her out. This boy had a lot of nerve since he made it completely obvious that he was examining her features.

"Hey, eyes up here!" she yelled as she pointed to her face. He ignored her comment and shrugged while he put his hands into his pockets.

"My dad's gonna move that," he said as he pointed the port-a-potty. "He's too busy shitting in the john." He paused when he noticed Jessie roll her eyes at him for cursing. " So he sent me here to warn ya but it looks you wanted some good ol' alone time in the crapper."

"I was just ..." Jessie started to say until she noticed he was staring at something down below.

"Too late," he said with a smile as he looked up.

Jessie gasped when she looked down immediately pulling her skirt down. When she had closed the door on her skirt, it made her skirt rise up. Now she knew the boy was ogling at her white cotton panties and she understood what he meant by "too late." Jessie had been so horny for the last few days and she had zero time to "polish her pearl." There was a huge wet spot on her underwear and she hoped that the boy assumed that it wasn't sex juices.

"Shoo, ska doodle," she said as she pointed off in a random direction. "Thanks for telling me about your dad and you can go while I wait."

He pretended not to hear her as he checked her out again. Jessie glared at him but that didn't make him stop. He quickly did an obscure hand signal with his hands which made Jessie look down and noticed a bulge growing in his pants.

 _Gee buddy, I know I'm attractive but keep it contained in your pants_ , she thought but by the boy's smirk, she realized she said it out loud. He took a step closer which signaled Jessie's reflexes, and the next thing she knew, the boy was lying on Zuri' bedroom floor.

"Holy Shit!" he exclaimed as he used his arm to prop himself up. "Some arm there."

"You're looking at a military daughter," she said as she folded her arms against her chest.

"I didn't mean any harm," he said as he stood up and took a few steps back. "It's just I _never_ saw a pretty girlie like you."

"That's what all pervs say."

"I'm serious - I really mean - I go to a Catholic all boys school," he studdered. "I never gotta chance to be around girls."

Jessie shook her head and said, "I don't believe you. I'm sure you made a sex bet with your fellow boy scouts on who could screw the most Manhattan nannies. I have half a mind to tell your dad what you did."

She noticed the boy soften, his shoulder slumped as he finally looked up at her eyes. "Don't do that," he pleaded. Jessie wasn't sure if he was being serious.

"All you're going to do is break girls hearts," Jessie said. "And stay away from my girls. I got kids to protect here. I bet you already chucked a bunch of girls and left them stranded on heartache island."

"Look, the only girl I ever been with was a daughter of a baptist pastor that I met at bible camp last summer," he began. "We banged and then she cried afterward."

"How did you screw that up?" Jessie asked as she raised her eyebrows.

"I shouldn't have boned such a prude," he answered in a matter-of-fact type of way. "All I wanted was to see why everyone I know is so anti-sex. I know why now. Sex fucking sucks."

Jessie sighed as she looked at the young man standing in front of her. He was blunt, disrespectful, and ill-mannered. Now she knew that he had spent his life repressing sexual desires and she could imagine that the people around him didn't exactly correct some of his less charming features. Jessie knew what it was like to grow up in a place that expected you to behave a certain way but failed to show you how to do so. She wasn't blaming this on the military or religion. She was blaming it on the people who cared more about using rules to punish instead of setting guidelines to help others. Of course, there was always room to take responsibility. She knew that she didn't always listen to others and she knew that the boy in front of her didn't as well. Jessie grew up thinking that no one understood her yet she realized that she never tried to understand anyone. Maybe the boy had the same problem.

Jessie thought about how the Rosses made her compassionate and self-less. They filled her life with meaning and made her accountable to someone. As she looked at the boy in front of her, she realized that he probably didn't have anything that made him accountable. He was drifting through life like she was. Using sex as a substitute for love - the love that you receive from family and friends. If only she could tell this boy what she knew. If only she could be a mentor to him and answer the questions that no one else would answer. The first thing she wanted to correct was his assumption about sex.

"Sex is awful with the wrong person," Jessie corrected.

"I know where ya going with this," he signed. "When I finally meet the woman I'm meant to spend eternity with-"

"Gosh no," she interrupted. "The right person is someone who respects you and makes you feel safe. Someone who knows what they're doing and someone who is not afraid to be told "no." The boy looked surprised and Jessie was glad that he was finally speechless. "You understand how consent works?"

"Consent?" he asked as he scratched his head. "Isn't that like giving permission?"

"Exactly," she answered. "Sex is only good when two people consent. If one person changes their mind and decides they don't want to do it, it's not consent. It's rape. If someone is pressured to have sex, that's called coercing. As long as both people willingly agree, then they are good to go."

Jessie studied the boy as she taught him one of the most important lessons about sexual intercourse. She didn't expect him to be a Tony and wait forever to tap someone's ass. She just wanted him to treat a girl with more respect. She hoped that the next time that he sees a girl he likes, he won't keep staring at her boobs. Jessie looked at him again and noticed that he must have been considering the things she said.

"And when you like a girl," she began. "Try not to make is so obvious that you're checking out her ass."

"How else would I know if she has a hot bod ?" he shot back.

"You wait! Listen kid, you're never going to hit a home run if you're staring her down the minute you meet her. Get to know her name first, shake their hand and during the conservation casually glanced down at their boobs. Make it quick like it was an accident. When she gets up and turns around, feel free to look at her nether region. Okay?"

"Got it."

"And always keep things slow - slower than slow. You never want a girl to think you're just using her to get laid. Be smooth and try to get her to make the first move. Always stare at someone directly in the eyes. It not only shows confidence but it makes it seem like you're not gawking at her."

The boy began looking irritated and he pulled out his android to check the time. He must have noticed Jessie glaring because he shot her an apologetic smile. He took a step closer to her, slowly as if he had been waiting for Jessie to punch him. When she didn't, Jessie noticed that his shoulders relaxed and he looked into her eyes again. She nodded in approval and smiled at her new student. She couldn't believe that she was teaching this strange un-named boy about "sex smarts." Someone had to teach him and it just turned out that Jessie had a gift for working with kids.

"That's great and all," he muttered before shouting, "How is that going to help me know what to do?" He must have noticed the confused look on Jessie's face before he added,"It's not like you're going to show me how to put my P in someone's V. Thanks for ya tips but I'm never gonna get any ass."

"I'll teach you."

"Huh?"

"How old are you?"

"Fourteen. Why does this matter?"

"I'm eighteen," Jessie said and she began to remember what Emma told her about New York's statuary rape laws when Emma tried to date an older boy. "In New York, a minor can have sex as long as the other person isn't more than four years older than them."

The boy stared at Jessie for a second before looking around the room. She watched as a cocky smile appeared on his face while his bulge grew more visible. He checked his cell phone before taking a step back from Jessie. She assumed that he was trying to figure out if she was serious. Jessie was completely serious about having sex with a fourteen-year-old boy just to teach him about having sex with a girl his age. She knew that a part of this was wrong but New York's law sort of permitted this. It's wasn't like she was coercing him or forcing him to do something that he didn't want to do. It was obvious that he was attracted to her and she was so horny that she was desperate for someone to "stick it to her."

"Would you like me to show you how to have sex?" she asked in a hushed voice.

"Yeah."

"Yeah, what?"

"Yes, I wanna have sex with you."

"Now remember, you can change your mind at any time."


	2. Chapter 2

For the first time, Jessie noticed that the boy didn't look impatient or bitchy. He looked shy and unsure what to do next. Jessie liked knowing that she was going to blow his mind and make him feel something that he never felt before. In high school, the boys never seemed to appreciate her sex and they never noticed how much better she was at sex than other girls her age. Now she had someone who would recognize her sexual prowess. She was going to take charge like she never did before.

As she glanced around Zuri's room, she didn't want to deprive any of Zuri's innocence by having sex on the little girl's bed. There was only one place that Jessie could use and that was the port-a-potty. She took a step inside of the tiny bathroom and gestured for the boy to come inside.

"In the loo?" he asked.

She nodded as the boy took a step inside the portable toilet. She closed the door as the small latrine grew dark. The boy pressed his back against the door and began fumbling with the sleeves of his shirt. Jessie could barely make out the boy's face but she could tell he looked like he was half excited and half nervous. She grabbed her cellphone from the waistband of her skirt and sat it on the seat behind her. The bright light of the phone allowed Jessie to clearly see the boy and it allowed him to clearly see her.

"Let's kiss," she instructed as she walked over to him, cupping the young teen's face.

She closed her eyes before pressing her lip against his. She parted her lips, placing them over her young lover's mouth. She could feel his heart pounding against her chest as the two engaged in an open mouth kiss. He panted against her mouth before she sucked his bottom lip. She placed a wet kiss on his cheek. Her soft lips easily glided over his smooth skin until she started kissing the crook of his neck. He thrust his pelvis against hers when she gently bit his soft flesh.

She moved away from him, smiling as she slid her hands over her blouse. She shook her hips as she untucked her blouse from the elastic band of her skirt. She teasingly raised her shirt up, only exposing the paleness of her stomach. She pulled her top over her head before she pulled down one of her black bra straps. She took a step towards the boy, giving him another open mouthed kiss.

"Fuck," he panted.

Jessie felt his hands roughly grab her breast.

"Hands off!" she barked as she peeled his hands off.

The boy said something sarcastic that Jessie didn't catch.

"This is how it's done,"she explained as she took his thumb and placed it over her bra cup, urging him to stroke it.

"I'll explode before I -" the boy exclaimed.

"I hate to burst your bubble but-" Jessie interrupted.

"That's what I'm sayin' "

"You have to hold it off."

She heard him scoff. She pulled her bra strap up, feeling a little frustrated with him. Jessie was going to allow the boy to have what he wanted but she was going to make him work for it. She looked at his shirt, realizing that he was way too overdressed.

"Take the shirt off," she commanded.

Jessie watched as he pulled his shirt over his head. In the dim light, Jessie could see that his arms were more muscular than his chest. She noticed that he eyed her bra for a second before quickly looking back up. Although he was a pain in her ass, he was a fast learner.

"Now what?" he asked. He acted like he was too afraid to take any initiative.

A cocky smile reappeared on his smug little face when Jessie dropped to her knees. He was about to unbuckle his belt until the Texan stopped him.

"Nice and slow," she reminded him.

Jessie was surprised that he didn't complain. Her eyes were leveled with his member as she closely watched him graze his fingers against his brown leather belt. She looked up at him, catching a glimpse of nervousness through his eyes when he stared at the nanny from this angle. His eyes darted away from the Texan when he finally unbuckled his belt. As he slowly slid his zipper down, Jessie caught a glimpse of his white briefs. He shot her another smirk when he reached down to pull his sneakers off his feet. Then, he tugged his jeans down to his knees, stepping out of them.

"You gonna remove the skirt?" he asked.

"No," she said before adding,"You can remove something else."

She stood up and slide her bra straps down her shoulders. Jessie turned around and pulled her long hair off her back. She pulled the condom from her bra as she waited for the boy to unclasp her wired undergarment. She tucked the condom under the elastic band of her skirt as she waited patiently for him to do something. She could feel tiny beads of sweat drip down her back as she started counting how long it was taking for him to undo her bra.

"Cold feet?" she asked.

"You said nice and slow!" he shouted as he hastily unclasped her bra. "I can't make ya happy. Can I?"

Jessie was actually surprised at his ability to swiftly remove a bra with one try. She held the cups against her breast before turning back around to face the boy. His eyes widen as Jessie brought her arms to her side, letting the bra slip off her slim body. The boy placed a hand on her shoulder before sliding his hand down to her breast. Jessie moaned when he stroked her hard pink nub. He started playing with her nipples, slowly circling them with his fingers and then licking around them.

"See, you can make me happy," Jessie finally answered. "Now it's my turn tor return the favor."

Jessie lowered herself onto her knees. She grabbed the legs of his briefs, sliding them down until his erect penis was fully visible. He was six inches long - a good size for a boy his age. She spat into her hands before she started stroking his member. She heard the boy gasp as she started moving her fingers up and down his length. She could feel beads of sweat against her forehand as she continued pumping him. She didn't realize how hot it was inside the port-a-potty. All she could focus on was listening to the beautiful grunts of the un-named boy above her. The boy moaned loudly when Jessie kissed his tip, her tongue probing inside of his hole. She tasted his salty pre-cum, humming to herself as she realized how much she missed servicing men.

"Damn," he panted.

Jessie couldn't hide her smile when she engulfed his head. She started bobbing her head up and down, increasing her speed. She looked up at the boy's lustful brown eyes as his dick slid farther down her throat. She fondled his heavy balls, feeling them tighten in her grasp.

"Bout ... to," the boy warned as hot cum exploded into the nanny's mouth.

Jessie sucked him dry as the boy recovered from his orgasm. She released his limp penis from her mouth and gave it a few pumps to help him become hard again. After a few strokes, Jessie stood up and gave her young lover a wet kiss. Her hard nipples were pressed against his sweaty chest as the two engaged in a passionate kiss. She hoped that he could taste himself as Jessie probe her tongue into his mouth. He ruffled her hair when he licked her lips, begging for entrance into her mouth. She opened her mouth, letting him swirl his tongue around. She definitely knew that he tasted himself now.

As she rubbed herself against his naked body, she could feel the outhouse begin to tip. The boy must have felt it too because he pushed Jessie back, still kissing her as he backed her closer to the toilet. The boy's instincts must have taken over because he placed a hand underneath her skirt. He pressed into her underwear, eliciting a moan from the Texas native. In the heat of the moment, the two rushed to pull off her panties. She didn't even remember if she urged him to take it off or if he just took the initiative to do so. All she could do was feel. She could feel his lips against hers; feel his arms wrapped around her torso, feel her naked breast against his bare chest, feel his member growing against the fabric of her skirt, and she could definitely feel the wetness between her legs.

Her heels slipped against the floor, making her fall onto the toilet seat and forcing the boy to tumble on top of her. She spread her legs when the two adjusted into a more comfortable position. She took his hand and placed it between her thighs. She moaned into his mouth when he brushed his finger against her opening. He repeated the same motion several times in a row, which made Jessie realize that this teaching session wasn't over.

She placed his hand on the hood of her crotch, silently urging him to touch it. She was too breathless to talk. Her heart was pounding so hard in her chest that she wouldn't be surprised if she had a heart attack. She tried speaking but her lips could only suck on his bottom lip. She could feel herself dripping onto the plastic toilet seat. His spongy lips were frantically capturing hers, making it difficult for Jessie to pull back. Finally, she was able to turn her head and uttered something under her breath. She assumed that he didn't hear it because his mouth had traveled down to her neck. As she moaned, she began to wonder if he was doing it on purpose. She kept urging him to play with her kitty yet he kept kissing her. Jessie felt his teeth nip her neck as his hands began fondling her boobs. This kind of torture was beginning to make it hard for Jessie to speak.

"Rub it," she instructed. She was so out of breath that she didn't even understand what she said. She took his hand off her breast and placed it back on her pussy. She grabbed one of his fingers, forcing him to stroke her clit. As she moaned, the boy finally understood what she wanted and started rubbing her sensitive little bud. She was feeling so much pleasure that the only thing she wanted to do was moan his name.

"What's ... your ... name?" she asked. She felt light-headed from talking.

"Leo," he responded.

"Leo," she moaned. "Finger me."

"I don't know -"

"Try."

He stood up and bent his back over. He placed a hand on the plastic toilet seat to steady himself. Jessie felt his fingers graze her entrance before he cautiously inserted his finger inside her. He added another finger as he slowly began pumping into her. He seemed to notice that he didn't receive any reaction from the nanny. He began to push farther down, increasing in speed until he heard Jessie moaned. Much to Jessie's irritation, he pulled his fingers out and shook his hand in the air. She assumed that his wrist was hurting. Lucky for him, she was ready to feel his member inside of her.

Before she took the condom out, the plastic part of the toilet seat cracked. She slid into the empty bowl, which was the part of the outhouse where the toilet water and waste went in. The room went dim when her phone fell into the toilet bowl.

"A little help here,"she said as Leo pulled her out, tumbling backward as she stood up.

She retrieved her phone, silently praying that the screen wasn't broken. She could feel sweat trickle down her body as she tried to figure out the safest place to sit her phone down. She needed some type of light in the tiny, stuffy latrine. She couldn't risk opening the door just in case Zuri had returned to her room. She sat her phone on the uncracked part of the toilet seat. The room grew brighter and she could focus her attention on the boy that was lying on the floor.

"Are you okay?" she asked and he nodded.

Her heels made a clink when she placed one foot near each of Leo's sides. His hard-on was standing up in the air when she grabbed the condom from underneath the elastic band of her skirt. The boy watched as she tore it open with her teeth, pulling the rubber out of its package.

"Aren't you on the-" he started to say before the nanny interrupted him.

"Always practice safe sex," she said. "Even if the girl is on the pill."

She hovered over Leo's member, lifting her skirt before lowering herself slowing onto him. She sank all the way down, enjoying the feeling of Leo deep inside of her. She began grinding her clit against his pelvic bone. Her breast started bouncing in Leo's face as she began sliding up and down his cock. Her heels were making a loud "clink" sound every time she bounced up and down. Her feet were beginning to hurt as the side of her feet rubbed against the leather straps of her heels. The two thrust against each other, making a "slapping noise" echo off the walls of the small latrine.

"I'm cumming!" she yelled as she came.

She used the last of her energy to continue riding him. She was slowly bouncing up and down as she waited for him to cum. After he came, she collapsed onto his chest. She rested her head against Leo's hot and sweaty chest. Her hair was damp from sweat but Leo still ran his hands through her brown locks. She closed her eyes and enjoyed the thing she loved the most. She loved when she was lying on top of a guy, allowing him to stroke her hair as he whispered sweet words into her ear. She realized how much she missed having a guy.

 _There's Tony,_ she thought. Tony wasn't the type of guy she could just sleep with. She knew that Tony was too much of a gentleman to sex her up this early in their relationship. She was glad that Leo was there to tie her over until Tony was ready to fuck Jessie.

Once the two were over their orgasmic bliss, they quickly got dressed. It was easy for Jessie to put her clothes on since she only had to put her bra and blouse back on. When they were finished dressing, Jessie opened the door. She closed the port-a-potty before pushing Leo against it to give him one last kiss.

"Thanks," Leo said before whispering the name, "Jessie."

"How do you know my name?" she asked.

She tried to remember if she had introduced herself to him. Her thoughts were interrupted when Tony and an unfamiliar Italian man walked into the room. Jessie was shocked to see Tony, who greeted her with his usual smile. She hoped that he didn't notice how flushed and sweaty Leo and Jessie were.

"Jessie," Tony said as he kissed her cheek. He put an arm around her and turned her body towards the man. "This is my father, Angelo. And it looks like you already met my brother, Leo."

Jessie froze as Leo shot her a smirk.

"That's how I know ya name," Leo said. "Because my brother can never stop talking about ya. And now, I know why."


End file.
